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"The really great ones are forgiving that way": 100 Baggers author on holding winners

13 lessons: why Berkshire was cut in half 3 times, why individual investors should stop checking their accounts, and why buying Monster Beverage at a 52-week high still paid 100x

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Nov 08, 2026
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Planet MicroCap · Nov 7, 2026 · 43m · 33m saved

With Chris Mayer, Co-Founder and Portfolio Manager of Woodlock House Family Capital and Author of "The Investor's Odyssey"

"The really great ones are forgiving that way": 100 Baggers author on holding winners

Berkshire Hathaway was the best performer among every US stock that rose 100-fold between 1962 and 2014, and it still got cut in half three separate times. Chris Mayer, who co-founded Woodlock House Family Capital and wrote "100 Baggers," told Planet MicroCap that finding those winners was never the main problem. Most investors focus on picking the right stock, while Chris says the harder part is sitting through the drawdowns once you own it.

"A lot of these winning stocks, the challenge was not so much... it's hard to identify them, of course... but even when you have them, to hold on to them is extremely difficult." — Chris Mayer

His new book, "The Investor's Odyssey," grew out of that research, and it borrows Homer's sirens as the name for everything that tempts an investor to sell too soon.

The full interview is covered here so you can skip it. 43 minutes of audio, 10 minutes of reading.

Here are the 13 lessons that matter.


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Key Takeaways

  • Even Berkshire Hathaway, the best stock in Chris's 100-bagger study, was cut in half 3 times

    • Apple and Amazon both suffered drawdowns of 60–70% or more

  • Knowing about behavioral biases does not make an investor immune to them, so Chris says exposure has to be cut by design, not willpower

  • Individual investors can beat professionals by not looking at part of their portfolio

    • Chris's father has held Intel, Microsoft and McDonald's for about 30 years each

  • Business quality comes before management, except in microcaps, where one founder can decide the outcome

  • With a great business, being early matters less than being right

    • Buying Monster Beverage at its 52-week high in several straight years still returned 100x

  • Chris's own weakness is selling too slowly, not too fast

1. Holding Is the Hard Part

Chris's new book started as a problem he noticed while researching "100 Baggers," which studied every US stock that rose 100-fold or more from 1962 to 2014.

Chris found that the biggest winners all went through deep drawdowns

"There's classic examples of Apple and Amazon... suffering 60, 70% plus drawdowns, but that actually is pretty common — these big winning stocks have many, many drawdowns." — Chris Mayer

Berkshire Hathaway, the top performer in the study, fell by half three separate times. Stocks can also go six years or more without passing their previous peak, a stretch that Robert Craft, who hosts Planet MicroCap, called the "Calypso" period.

2. Where the Odyssey Came From

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